In the late Middle Ages, Italians used the figure of fortuna understood as working in tandem with divine Providence to discuss the contingency of future events. Presiding over a relentlessly turning wheel, Fortuna provided a moral education for humanity, demonstrating the transitory and ultimately worthless nature of worldly success and possessions in the face of the promise of eternity. This chapter examines the deep foundations of this figure in Boethius’s Consolation of Philosophy (written in the sixth century CE), tracing its continuing influence into the fifteenth century. It argues that the moral allegorical figure constructed by Boethius underwent subtle changes in the works of early Italian humanists. Through a close analysis of several texts written between the mid-fourteenth and mid-fifteenth centuries, the chapter demonstrates how the bonds that tied the figure of fortuna to Providence began to loosen, laying the foundations for new explanations for future contingency disconnected from the temporality of Christianity.